Work

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[ j ]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

Year: 2024

Type: article

Abstract: Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45–90%). This cascade involves an initial Suzuki–Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C–H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[ j ]fluoranthenes, which are all structurally relevant to benzo[ j ]fluoranthene-based fungal natural products. The effectiveness of our strategy was demonstrated via a concise, four-step synthesis of the tetramethoxybenzo[ j ]fluoranthene derivative 18 , which represents a formal total synthesis of the fungal natural product bulgarein.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.20.273

Authors: Merve Yence, Dilgam Ahmadli, Damla Surmeli, Umut Mert Karacaoğlu, Sujit Pal, Yunus Emre Türkmen

Institutions: Bilkent University, National Nanotechnology Research Center, Universidad Nacional Autónoma de México

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Türkiye Bilimsel ve Teknolojik Araştırma Kurumu, Bilkent Üniversitesi

Award: Trunkaton C ve Daldinon B Doğal Ürünlerinin Total Sentezi